New 8-Oxabicyclo[3.2.1]oct-6-en-3-one Derivatives with Plant Growth Regulatory Activity †
✍ Scribed by Demuner, Antonio J.; Barbosa, Luiz C. A.; Veloso, Dorila P.
- Book ID
- 118176495
- Publisher
- American Chemical Society
- Year
- 1998
- Tongue
- English
- Weight
- 86 KB
- Volume
- 46
- Category
- Article
- ISSN
- 0021-8561
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This work describes the conformational analysis of alcohols 2a,4a-dimethyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3a-ol ( 5) and -3b-ol (6) and of alcohols 1,2a,4a,5-tetramethyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3a-ol (7) and -3b-ol (8). Based on NMR data and AM1, HF
irradiation of 8-oxabicyclo[3.2.l]oct-6-en-2-ones results in a 1 ,Sacyl rearrangement. The initial photoproduct undergoes a subsequent reaction involving hydrogen transfer followed by intramolecular cycloaddition of a ketene intermediate.